Triethylamine → (S)-cyanomethyl 2-methoxy-3-phenylpropanoate

HRID 1482190Notes

Reaction equation

HRID 1482190 reaction equation
[CH3:1][O:2][C@@H:3]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:4]([OH:6])=[O:5].Br[CH2:15][C:16]#[N:17].C(N(CC)CC)C>C(#N)C>[CH3:1][O:2][C@@H:3]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:4]([O:6][CH2:15][C:16]#[N:17])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11534BromoacetonitrileHCID 11858535(S)-2-Methoxy-3-phenylpropanoic acid2×

Product 1

HCID 89668408(S)-cyanomethyl 2-methoxy-3-phenylpropanoateYield 71.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(S)-2-Methoxy-3-phenylpropanoic acid (Compounds 7a, 0.50 g, 2.50 mmol) and 2-bromoacetonitrile (1.20 g, 10.00 mmol) were dissolved in acetonitrile (60 ml). Then triethylamine (0.50 g, 4.99 mmol) was added dropwise under ice-cooling. After stirring at room temperature for 40 minutes, the reaction solution was concentrated under reduced pressure, and the residue was purified by column chromatography (petroleum ether:ethyl acetate=20:1) to afford the title compound (0.39 g, 65%).

Workup

  1. temperaturecooling
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. customthe residue was purified by column chromatography (petroleum ether:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-d7043f02869940079dc2a1e9377de8e5
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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